Manufacture of ortho-anisidine and similar aminophenol ethers



35 steam it may I tion by distilling it from the aqueous liquid atented tiller JOSEPH 'I'CHERNIAC, F STREATHAM HILL, LONDON, ENGLAND IITAN'UJBACTURE 0F ORTHO-ANISIDINE AND SIMILAR AMINUPHENOL ETHEJELS 1N0 Drawing. Application filed September 29, 1927, Serial No. 222,940, and in Great Britain octo'ner 52, 1826.

This invention consists in the manufacture of ortho-aminophenol ethers by heating in a solution of an alkali, the product of reaction of an alkyloxyarylcarboxylic acid amide 5 with a hypochlorite.

By the action of hypochlorite on methylsalicylamide, Pinnow and Miiller (Berichte 1895, vol. 28, page 158) could detect only a faint smell of carbylamine andfailed to 10 obtain any ortho-anisidine.

The reason of their failure appears to be that when methylsalicylamide is treated with alkali hypochlorite at ordinary temperature, there is first formed a monochloramide which remains in solution as an alkali salt:

If, however, the solution is heated, in the presence of caustic alkali, carbon dioxide is formed, and ortho-anisidine'is produced:

C lLOCH CONGlNa-t NaOH-l-HJ) C ILOCEL,.NH +NaCl+ NaHCO The processof the invention is best con ducted by treating the alkyloxyaryl-carboxylic acid amide with a solution of a hypochlorite containing a caustic alkali and heating the mixture. Preferably the amide is first dissolved in a solution of alkali hypochlorite, containing the necessary quantity of caustic alkali, and the whole heated; The ether is removed from the aqueous liquid and purified in known manner; or if volatile with be isolatedin purified condicontalning it. a

The following example illustrates the invention:

15.1 kilos of methylsalicylamide are stirred with 1500 litres of a solution of sodium hypochlorite containing 8.8 kilos of NaOCl and 4 kilos of caustic soda dissolved in 18 litres of water. The mixture is kept at about 20 C. for a few hours and then heated to boiling. The anisidine is steamdistilled and goes over practically pure. The yield is over 80 per cent.

Having thus fully described the nature of the said invention and the best means I know JOSEPH TUHERNIAU. [as] 

